[ CAS No. 7368-78-7 ]

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2D
Chemical Structure| 7368-78-7
Chemical Structure| 7368-78-7
Structure of 7368-78-7

Quality Control of [ 7368-78-7 ]

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Product Details of [ 7368-78-7 ]

CAS No. :7368-78-7MDL No. :MFCD00051937
Formula :C7H7BrO2Boiling Point :250.1°C at 760 mmHg
Linear Structure Formula :CH3OHOC6H3BrInChI Key :-
M.W :203.03Pubchem ID :262234
Synonyms :

Computed Properties of [ 7368-78-7 ]

TPSA : 29.5 H-Bond Acceptor Count : 2
XLogP3 : - H-Bond Donor Count : 1
SP3 : 0.14 Rotatable Bond Count : 1

Safety of [ 7368-78-7 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 7368-78-7 ]

  • Upstream synthesis route of [ 7368-78-7 ]

[ 7368-78-7 ] Synthesis Path-Upstream   1~12

  • 1
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  • [ 7368-78-7 ]
YieldReaction ConditionsOperation in experiment
95% With tetra-N-butylammonium tribromide In dichloromethane at 23℃; for 2.00 h; General procedure: A solution of NBu4Br3 (1.0 eq) in CH2Cl2 (~5 mL per mmol NBu4Br3) was added immediately to a solution of a phenole 1 (1.0 eq) in CH2Cl2 (~ 5 mL per mmol 1). The reaction mixture was stirred at 23 °C for 2 h. The solvent was removed under reduced pressure (12 mbar, 40 °C). Water (5.0 mL) was added to the residue and the aqueous layer was extracted with Et2O (3 * 10 mL). The organic layer was separated and dried (MgSO4). The organic solvent was removed under reduced pressure (14 mbar, 40 °C) to leave an oily residue, which was purified by adsorption chromatography (SiO2, CH2Cl2).
95% With N-Bromosuccinimide In acetonitrile for 0.50 h; N-Bromosuccin I self-imide (180 mg, 1 mmol)Add to guaiac acid (124 mg, 1 mmol, Structure 1)In acetonitrile (20 mL);After stirring for 30 minutes, the reaction was quenched with saturated sodium thiosulfate solution,Ethyl acetate extraction three times; the combined organic phase, washed with saturated saline,Drying over anhydrous sodium sulfate and removal of the solvent under reduced pressure give the crude product,Column chromatography (ethyl acetate: petroleum ether, 10: 1),The product 4-bromo-2-methoxyphenol was obtained in a yield of 95percent.
91% With N-Bromosuccinimide In N,N-dimethyl-formamide at 0℃; for 0.50 h; Inert atmosphere To a stirred solution of 2-methoxyphenol (5.00 g, 40 mmol) in DMF (25 mL) under an atmosphere of nitrogen at 0 °C, was added a solution of N-bromosuccinimide (7.2 g, 40 mmol) in DMF (25 mL). The resulting mixture was stirred for 30 min. Ice cold water (50 mL) was added and the mixture was warmed to room temperature. The aqueous mixture was extracted with diethyl ether (3 * 30 mL) and the combined organic extracts were washed with water (50 mL), brine (50 mL) and then dried (Na2SO4). The crude product was purified by flash chromatography (3:1 hexanes/ethyl acetate) to give the title product 8 (7.41 g, 91percent) as a yellow oil. 1H NMR (300 MHz; CDCl3) 3.87 (3H, s, 2-OCH3), 5.70 (1H, br s, OH), 6.78 (1H, d, J = 6.2 Hz, 6-H), 6.98 (2H, m, 2 * Ar-H); 13C NMR (75 MHz; CDCl3) 56.2 (OCH3), 111.5 (C-4), 114.1, 115.7 and 124.1 (Ar-CH), 144.8 (C-1), 147.2 (C-2). The 1H and 13C NMR data were in agreement with the literature values
78% With N-Bromosuccinimide In N,N-dimethyl-formamide at 0℃; for 0.50 h; A solution of NBS (1 eq.) in DMF (50mL) was added dropwise to a solution of guaiacol (1eq.) in DMF (50mL) at 0°C. After being stirred for 30min, the reaction mixture was quenched with ice water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and then evaporated to dryness under reduced pressure. The residue was further purified by column chromatography over Silica Gel 200–300N (petroleum ether/ethyl acetate 9.5:0.5) to give 10a as an oil (78percent).

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  • 2
  • [ 6689-37-8 ]
  • [ 7368-78-7 ]
YieldReaction ConditionsOperation in experiment
84% With tris(2,2'-bipyridyl)ruthenium dichloride; carbon tetrabromide In acetonitrile at 20℃; Irradiation General procedure: To a 10 mL round bottom flask equipped with a magnetic stir bar were added phenols or alkenes (0.1 mmol), CBr4 (33 mg, 0.1 mmol), dry CH3CN (1 mL) and Ru(bpy)3Cl2 (3.8 mg, 0.005 mmol). The mixture was irradiated with blue LEDs (1 W) at room temperature open to air until the starting material disappeared completely (monitored by TLC). After the reaction was completed, the solvent was concentrated in vacuo. The residue was purified by flash column chromatography to give the final product.
Reference: [1] Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 622 - 627
  • 3
  • [ 90-05-1 ]
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  • [ 28165-49-3 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 15, p. 1877 - 1878
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  • 4
  • [ 138505-27-8 ]
  • [ 7368-78-7 ]
Reference: [1] Journal of Organic Chemistry, 1998, vol. 63, # 24, p. 9139 - 9144
  • 5
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  • [ 53948-36-0 ]
Reference: [1] Journal fuer Praktische Chemie - Practical Applications and Applied Chemistry (Germany), 1999, vol. 341, # 1, p. 59 - 61
  • 6
  • [ 90-05-1 ]
  • [ 7368-78-7 ]
  • [ 37942-01-1 ]
Reference: [1] Synthesis, 2010, # 10, p. 1629 - 1632
[2] Synthesis, 2010, # 10, p. 1629 - 1632
  • 7
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  • [ 28165-49-3 ]
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Reference: [1] Dalton Transactions, 2013, vol. 42, # 33, p. 11926 - 11940
  • 8
  • [ 90-05-1 ]
  • [ 7368-78-7 ]
  • [ 37942-01-1 ]
  • [ 53948-36-0 ]
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[2] Journal of Organic Chemistry, 1997, vol. 62, p. 4504 - 4506
  • 9
  • [ 376396-10-0 ]
  • [ 151-10-0 ]
  • [ 7368-78-7 ]
  • [ 557757-32-1 ]
Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 18, p. 9367 - 9383
  • 10
  • [ 54145-18-5 ]
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Reference: [1] Synthetic Communications, 2008, vol. 38, # 21, p. 3823 - 3833
  • 11
  • [ 151-10-0 ]
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  • [ 123-72-8 ]
Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 18, p. 9367 - 9383
  • 12
  • [ 63057-72-7 ]
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Reference: [1] Monatshefte fuer Chemie, 1963, vol. 94, p. 753 - 760
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